Elaine Wherry: Why I Now Believe the Glass Ceiling Is Real

Once a naysayer about gender discrimination, this conference speaker shares how she experienced it first hand and came to the conclusion that the glass ceiling is higher than she thought it was.

By Elaine Wherry (Co-founder & CxO, Meebo)

Until three years ago, I thought the question of whether gender matters at startups was a ridiculous proposition. Startups are founded on meritocracy and engineering objectivity – the perfect place for anyone with elbow grease to succeed. Our heroes are the underdogs who encounter a thousand setbacks before a single success. A startup is already grueling — why hunt for additional problems that are at best, irrelevant and at worst, manufactured? And as a co-founder, it’s your responsibility to shape an inclusive culture through thoughtful hiring and leadership. If bias exists, it’s your own doing.

Even though my feminist mother had tried to convince me otherwise, I rolled my eyes at these outdated gender debates. The world had moved on. There were more pressing issues at hand. But then one personal experience reversed my thinking entirely.

It happened almost three years ago, while I was trying to make my way through the crowd at South by Southwest to reach a ballroom where I was going to lead a panel. I received a call from my senior director-to-be — the rock star I’d found and wooed after an exhaustive year-long search. His arrival was just days away, and I’d already invited him to product meetings, introduced him to key team members and strategized first hires with him. He told me he wouldn’t be joining my startup.

My stomach sank. The 1,000-person ballroom a hundred yards ahead faded away, as I asked why he was turning us down. He told me that the reason was — me.

He outlined a few specifics — I’d taken two to three days to give feedback to his presentation. My energy level in our last meeting had given him pause. But even when I pressed for more detail, he reiterated that it wasn’t just one particular thing but rather a general sentiment that had accumulated with time. Despite our signed offer, he had already accepted another position. This was goodbye.

I put the phone in my pocket. I needed privacy. I walked until I found myself underneath a bridge surrounded by broken beer bottles and an abandoned office chair. I started to call the team but my throat choked and I collected myself before trying again. My co-founders were disappointed and angry. Months prior, I’d already had one senior lead join and leave after six months when he realized a startup wasn’t for him. I’d spent my get-out-of-jail-free card and I could hear their judgment crystallize: “Well this proves it. She’s just not a senior operator.” There were no words to convey how unbelievably, profoundly sorry I was. But I offered: “It’s a long shot, but if it’s really me, ask him to consider reporting directly to Seth,” my co-founder and CEO.

The suggestion had unspoken but understood repercussions. I had already floated the possibility of stepping away from the company but it was still a, “Hey, let’s see where things are next year.” Without this report, my exit was certain. The business couldn’t afford another setback and with my insistence, the team agreed.

Under the bridge, I took a deep breath and resumed my ballroom walk while the California team scrambled. As I stepped onto the stage with a brave face, I had the bittersweet realization that if my co-founders succeeded, this would likely be my last SxSW conference representing Meebo. And sure enough, later that night, my co-founder called to say he’d been successful. After lengthy negotiations including a bump to VP, an increase in salary and signing bonus, the rock star senior director re-joined. I was relieved yet crestfallen. My last official Meebo day would be six months away.

Many weeks later, I recounted the story to my coach. I expected, “Elaine, here’s some feedback…” or “Did you consider this reporting structure…?” But her follow-up caught me off-guard. “How old and where’s he from,” she asked.

I responded and she continued: “Right, well, it’s because you’re young and female.” We’d never discussed gender before and I’d assumed she thought the debate was nonsense, too. Instead of, “Yes, you could have handled this better” her tone was, “How could you be so naïve? You just got blindsided by the old boys’ club. Older men don’t want to report to young females!”

This was not about merit, whose code was better, reasoned debate or building the best product. This was a political land grab spurred by a perception of female weakness. I’d acquiesced too soon and it was still my fault, but for a very different reason.

I was speechless. Sure, gender biases probably existed somewhere, but not in startups and certainly not in my startup. For years, I’d belittled these gender debates. But by being so defensive, I’d backed myself into a corner and out from the team.

The glass ceiling exists; it’s just higher than I’d realized. As a co-founder, your role is to attract the best talent to compete in the market. For executives, you want experience and that comes from previous generations who weren’t readily exposed to senior women and minority groups. By nature, we like people who are like ourselves and, even if it’s subconscious, finding an exec who will report to a young female long-term is harder than finding someone who will report to a like-minded male. Instead of, “The world is so unfair!” I wish the conversation had been more pragmatic: “Of course you can do this but at this startup stage, be ready to show some teeth and work even harder.”

Regardless of the reason, when you can no longer attract and lead the best talent, you’re no longer the right person for the role.

It’s easy to see why diversity is hard. Diversity fosters innovation and resilience – everything young startups need to succeed. But as the business matures, values shift. Investors need predictability and security. And when it’s “succeed or die,” diversity takes precious time and resources – whether to reconcile differing styles, to second-guess our initial assumptions, to run an egalitarian hiring process or even to give a co-founder yet another shot. But once a selection bias is baked into the culture, it’s self-reinforcing and difficult to reverse. Even within my own startup and with culture as one of my direct purviews, I couldn’t prevent the squeeze.

The answer is not hiring quotas or prettier bathrooms. It’s strong leadership. Diversity only makes sense if you can harness the multitude of strengths and perspectives to the business objectives. That’s a skill that benefits everyone, regardless of demographic. But if long-term diversity depends upon leadership skills, then inexperienced founders with good intentions might be surprised that their company has grown one-dimensional.

Now that I understand the structural underpinnings, I’ve joined the chorus that I once shunned: Yes, this is real; it’s a generational gap that extends beyond women, and it affects everyone. Even when I differ on technicalities, I no longer roll my eyes or ask when this debate will finally die. When the young women around me grumble: “Elaine, can you believe this? By bringing up gender again, they’re making it an even bigger issue,” I cut them short. It’s because our industry doesn’t fully grasp the problem and we need more people to legitimize the cause to be taken seriously.

Don’t be a naysayer. Of course you’re a smart, strong, capable woman and you can do this but watch out. The hard work of the women who fought before us has paid off but it hasn’t yet penetrated the very top layers. It’s up to us to continue their efforts and with a bit more time and determination, write this final chapter.

Do you believe in the glass ceiling?

About the guest blogger: Elaine Wherry co-founded and served as chief experience officer of Meebo, a company that enabled of users to chat, share and connect with their online friends before being acquired by Google in 2012. Today she advises aspiring entrepreneurs and startups, publishes thoughts on entrepreneurship on her blog ewherry.com, and is taking a quick breath before diving into her next endeavor.